Basic ether of resorcinol



Patented Apr. 30, 1929.

UNITED STATES PATENT OFFICE.

HANS HAHL, OF ELBERFELD, GERMANY, ASSIGNOB TO W'INTHROP CHEMICAL COH- PANY, INCL, NEW YORK, N. Y., A CORPORATION OF NEW YORK.

BASIC ETHER O]? RESOBCINOL.

No Drawing. Application filed August 13, 1927, Serial No. 212,841, and in Germany September 20, 1926.

The present invention relates to new basic ethers of resorcinol, more particularly to compounds of the general formula:

ox I wherein X, R R and R stand for alkyl groups.

These compounds are obtainable according to the usual processes for the manufacture of alkyl ethers. Preferably a basic alkyl-haloganide, as for instance, diethylamino-ethylchloride, may be caused toreact with a mono-alkyl ether of resorcinol in the presence of an alkaline acting agent.

The new products possess a strong contracting action on blood vessels and a labor pain exciting action. They are generally colorless or slightly yellow colored oils of basic odor which can be distilled in a vacuum without decomposition, being diflicultly soluble in water and easily soluble in acids.

The following exam les serve to illustrate my invention, all parts eing by weight Emampl 1.-- parts sodium are dissolved in 400 parts alcohol and treated with 100 parts resorcinol-mono-methyl ether. The reaction mixture is heated for about two hours to about 100-120 0., with 125 parts diethylamino-ethylcliloride. After distilling ofl the alcohol the residue is treated with water, the resglting oil separated, dried and fractionate The compound thus obtained boils as a colorless liquid at 160-166 C. under a pressure of 13 mm. It gives with hydrochloric acid a crystalline salt which melts at 138-140 C.

Example 2.40 parts resorcinol-monomethyl ether are treated with a solution of 8 parts sodium in 300 parts alcohol and heated for about three hours to about 80100 C. after the addition of 60 parts a-dimethylamino-B-methyl- -chlorobutane of the formula:

After distilling of! the alcohol the new strong contracting basic ether is separated with water and frac; tionated after drying. It distills at 170-172 C. (12 mm. pressure) as a colorless oil and possesses the following constitution:

OCH:

Example 3-3.5 parts sodium are dissolved in 100 parts alcohol and heated together with 20 parts resorcinol-mono-ethyl ether and 20 parts dietl1ylamino-ethylchloride for about five hours to about 100-110 C. When the reaction is com lete the product is worked up as described 1n Example 1. The new base distils at 17 1-17 9 C. under 12 mm. ressure as a yellow liquid which is easily so uble in wherein X, R R and R stand for alkyl groups.

2. As new products the compounds of the general formula:

wherein X, B and R stand for methylor ethyl-groups and R, for an alkyd group containing at least two but not more than five carbonatoms, which are slightl yellow colored oils of basic odor, difiicult y soluble in water, easily soluble in acids, possessing 9. action on blood vessels and labor pain exciting action.

3. As new productsthe compounds of the general formula:

wherein X stands for a methyl-. or ethyl- 10 group, which are slightly yellow colored oils of basic odor, diflicultly soluble in water, easily soluble in acids, possessing a strong contracting action on blood Vessels and labor pain exciting action.

4. As a new product the compound of the general formula:

OCH:

CIHI

forming with hydrochloric acid a crystalline salt melting at 138 to 140 C. and possessing a strong contracting action on blood Vessels and labor pain exciting action.

In testimony whereof I have hereunto set my hand.

HANS HAHL 

